Triethylamine → HCID 19756114, compound

HRID 1587701Notes

Reaction equation

HRID 1587701 reaction equation
[CH2:1]([C:12]1[CH:13]=[N+:14]([O-])[CH:15]=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:19]([N:21](CC)CC)C.C(C1C=CC(CCCCCCCCCCC)=CN=1)#N>C(#N)C>[C:19]([C:13]1[C:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:17][CH:16]=[CH:15][N:14]=1)#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19756128HCID 19756128, compoundHCID 54296806HCID 54296806, compound

Product 1

HCID 19756114HCID 19756114, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 10.0 g (40 mmol) of 3-n-undecylpyridine N-oxide and 8.10 g (80 mmol) of triethylamine dissolved in 40 ml of acetonitrile was added 15.8 g of trimethylsilyl anilide, while stirring, at room temperature. After the dropwise addition, the mixture was refluxed for 66 hours and concentrated under a reduced pressure, followed by silica gel column chromatography (ethyl acetate:hexane=15:85), to give two kinds of solids A (4.40 g) and B (4.10 g). From the data of NMR, A was determined to be 2-cyano-5-n-undecylpyridine, and B the desired 2-cyano-3-n-undecylpyridine (yield 38.8%).

Workup

  1. additionAfter the dropwise addition
  2. temperaturethe mixture was refluxed for 66 hours
  3. concentrationconcentrated under a reduced pressure
  4. customto give two kinds of solids A (4.40 g) and B (4.10 g)

Sources & evidence

ORD record
ord-74a8bf7c872049ce801c6b8c19886750
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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